Six Mistakes That Successful Leaders Make

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As an executive coach, my client relationships are some of the most rewarding aspects of my job. Generally, they are highly successful, driven and focused people. They tend to think creatively and expansively.

They routinely experience what most others rarely do if ever: The act of creation. The ability to generate a novel idea and see it through to a fruitful completion.

However, success comes with blind spots. This isn’t unique to the successful. We all only have eyes on the front of our heads. We all are blind somewhere.

The unique challenge with the blind spots of the successful are that they are shared by fewer people, so they are less recognized, understood or, frankly, empathized with.

It’s important to understand these though to avoid the dynamics that lead to the slide and failure of hugely successful, can’t fail, “everywhere” businesses like Kodak, RadioShack, and Blockbuster.

Six Blind Spots of Successful Leaders

Isolation As leaders become more successful many find that they are surrounded by fewer and fewer people with whom they are peers. Some interpret this with the platitude: “It’s lonely at the top.”

They often, also, isolate themselves from the people they lead. It is the norm for executives to tell me, “We’d like to make X changes, but our people just won’t support it.”

Then when I talk to their staff, I find that they are waiting, in frustration, for their leaders to make those changes. Leaders are often far more afraid of change than the staff. The staff is more concerned about how change is implemented and what the impact can be. Isolated leaders will never be able to discover or address these concerns.

This is a very dangerous perspective to take on. Isolation tends to breed errors in perspective and judgment.  Isolation leads to choices that don’t match an accurate perspective of your environment.

It becomes an important discipline to intentionally surround yourself with people who inspire you and challenge you. I can attribute most of my business success with intentionally finding and joining a community of consultants who operate at a very high level. To be honest, they can be very uncomfortable to be around because they constantly challenge my assumptions and ways of doing things. However, listening to them produces significant year over year growth.

It is also an important discipline to engage with those you lead and your customers. If you are always perceived as Moses Coming Down from the Mountain people will be intimidated. Their communication increasingly becomes self-edited.

Superstition As a sociology undergrad it was drilled into my head that “Correlation does not mean Causation.”  Just because every time you pass a sign that says, “Moose Crossing” and a moose steps out onto the road doesn’t mean that your driving past the sign is what triggered that event.

Superstition is to falsely and rigorously attribute an unrelated cause to any result.

Successful leaders can be enormously superstitious. They tend to attribute incorrectly how their success was created, failure avoided or disaster averted.

This can be difficult for leaders to accept. Particularly when facing a need for a significant organizational change. Even though change is needed, there is a strong belief that doing things the old way will generate new, different results.  This is often tied to the comfort of knowing how to produce results within a certain context.

It can also be tied to the fear of the unknown. Successful leaders usually have experience navigating the unknown, but their current experience is mostly with navigating the known. It can be very challenging to encourage them to step outside of what is known, again, and take new but necessary risks.

Entitlement Many leaders have worked very hard for their success. They also have given a great deal for their employees. If you are a leader in the non-profit community or in public service you may have sacrificed for the benefit of those you serve.

This can produce a sense of entitlement. The sense of, “I deserve this.” It allows us to excuse choices and behavior that otherwise we wouldn’t have excused. These can look like inappropriate ways of relating to others. It can look like taking inappropriate advantage of people or situations. It, also, often leads to self-medication or addictive behaviors.

Resentment Success often holds surprises for people. It comes with challenges. Because you are successful, you aren’t as likely to experience empathy or support when facing those challenges. People that you suffer holistically.

Additionally, there are new demands or expectations placed on you. These are often both real and perceived. There are real, new demands and expectations. However, leaders can also project these as well – inaccurately believing that certain things are demanded or expected.

So, leaders become resentful.

Resentment can often lead to entitlement. See above.

Deprivation This is a slightly less common trap, but it is still common enough. Particularly for leaders who were used to hard work, long hours, nose-to-the-grindstone, pull-yourself-up-by-the-bootstraps ethic.

They don’t know how to quit. It’s like they’ve never really understood what 4th or 5th gears are for on their car. So, they push and strain and redline.

This relates to some of the superstitions above. Because hard work got them here, there is a strong belief that equally, sustained effort is what will make them successful.

Instead, they often run the risk of burning themselves out. Becoming resentful. Feeling entitled.

Stress Many successful leaders assume that the answer to most questions is a broader pair of shoulders. The adrenaline, the crisis, the urgency all provide energy and focus for the successful leader. Stress can function as its own addictive experience.

For many leaders, calm or peacefulness feels disordered or unnatural. This often has roots back into their family of origin.  I’ve watched leaders become visibly uncomfortable when in calm or quiet environments. They’ll fuss around with something until they’ve achieved commotion. Then things feel right again – even if they feel frustrated and stressed.

Prevention and Escape from These Traps

Engagement & Accountability

Isolation is the environment that most of these traps are found in. Putting effort into finding and building relationships with a diverse group of peers is incredibly helpful, particularly if you are with peers who are actively pursuing their personal and professional growth. Many leaders find tremendous value in peer mentoring groups.

Additionally, ensuring that there is always at least one or more people, whom you respect and look up to, who you build a mentoring relationship with. This can look like hiring a coach. But I’m more specifically referring to organic relationships. Just the experience of reaching out and trying to build a relationship with someone, for your growth, begins to sharpen you again.

Cultivating Emotional and Spiritual Health

For many successful people, the drive for success can have roots in past issues. Where some people were shut down by a tough background, others propelled themselves forward due to their backgrounds. This dynamic is common enough that it is worth exploring. This can emerge as a sense of not being enough, needing to prove ones-self, growing up in poverty, etc.

It can look like not being able to feel successful if you are. It can feel like the inability to relax

These are never fun things to look at or discuss. At a certain point in everyone’s life, though, these old hurts stop becoming fuel for success and start to become leashes holding us back.

After some time, leaders who are objective will see there are unhelpful patterns in their leadership relationships. One of your best financial and time investments might be working on your “stuff” with a skilled counselor or minister.

Make sure they are skilled. Feel free to try a few people out until you find a good match for yourself. You don’t have an obligation to them. At most, you have an obligation to the process and to the people you lead.

Are you susceptible to one or more of these traps? What will you do to free yourself?

Take good care,


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